Most of the time, reading a novel is pretty straightforward. Step one: pick up book. Step two: open book. Step three: read, and enjoy. Some novels, though, go beyond mere complexity and actually require you to be knowledgable in a certain area just to have hope of enjoying—or understanding—what’s on the page. These five books are perfect examples: if you’re going to read one of them, you’d be well advised to dig through a long list of required reading first, or you’ll miss out on half of what they have to offer.

Silverlock, by John Myers Myers
The only character in Myers’ fantasy who isn’t a famous figure from classic literature is the protagonist, A. Clarence Shandon, MBA. Hailing from Wisconsin, Shandon shipwrecks in the Commonwealth of Letters, where he is befriended by Golias and meets Pathfinder, Puck, Becky Sharp, Brian Boru, and dozens of other (hopefully) familiar names as he goes on an adventure that transforms him from a rather full-of-himself academic into a legend in his own right, nicknamed Silverlock. If you didn’t recognize every one of the names in the previous sentence, you’ll need to bone up on your literature and history before diving into this dazzling novel—every single reference is a play on famous and not-so-famous books, offering shades and deep dives that go far beyond the basic plot.

The Eyre Affair, by Jasper Fforde
In order to truly understand everything Fforde does in his excellent Thursday Next books, it would, first of all, help tremendously to be British, as many of Fforde’s references are specific to his home country, although attempts are made to Americanize them for U.S. audiences. Even more important for a book series set in a universe in which literature is as popular as superhero movies and is also something dynamic that has to be managed—often by jumping into the stories themselves—is the long list of novels you’ll need to bone up on if you’re to have any hope whatsoever of understanding the jokes, references, puns, and lampshadings that come at you fast and furious in this deft, intelligent metafictional masterpiece.

Special Topics in Calamity Physics, by Marisha Pessl
Every chapter in this impressive novel is named after another novel, and more literary references abound; the whole thing is structured like a college course, complete with voluminous footnotes. That alone requires that you do a lot of reading before diving in, but more importantly, Pessl includes plenty of references to works that don’t actually exist, making the novel even more absorbing as she transcends mere name-dropping to creating her own half-fictional literary world. If you’re going to be able to tell when she’d referencing a real work and when she’s created something purely for her novel, you’re going to have to have a pretty deep knowledge of novels, plays, and historical works at your disposal. Once you’ve done the reading, the central mystery of Pessl’s novel, set largely in a film studies department at a small college where the teacher dies by apparent suicide, becomes even more engrossing.

Just About Every Stephen King Book Ever
Stephen King has evolved from a purveyor of horror stories into a national institution, and his fiction has evolved right along with him, creating one of the most complex interrelated meta universes in history. Over the years, King has painstaking retrofitted all of his works into a single, awe-inspiring world. Characters and events are referenced in different novels, stories are tied together in surprising ways, and motifs and symbols appear in unexpected places. In fact, there are some beautiful (and complicated) infographics out there designed to clarify the whole King universe for you—although tracing the connections might require some time, patience, and a magnifying glass of some sort. The epicenter of King’s universe is definitely The Dark Tower series, which pulls in so many characters, events, and tropes from his other books that the King Metauniverse simply doesn’t make any sense without it.

Gravity’s Rainbow, by Thomas Pynchon
The list of topics that you should have more than a glancing knowledge of in order to have half a chance with this novel includes statistics, world history, linguistics, and physics. And that’s just for starters. Even if you do go back to school and spend 10 years with your nose in various ancient tomes of forgotten lore, you still might not get everything that Pynchon is serving up here. Gravity’s Rainbow is one of those novels that divides people into two camps: those that think its genius even if they can’t quite get it all, and those who think it’s impenetrable. If you want to make up your own mind about it, though, you have to at least give yourself a fighting chance, and that means creating a lengthy syllabus and reading until you’re at least half as smart as Pynchon himself.

Life’s not getting any easier—and neither are these books. While there’s nothing wrong with reading a brisk spy novel or a weepy romance or a horror novel you have to put in your freezer at night in order to be able to sleep, you know you’ve been avoiding certain novels your whole life. Time to put on your grownup pants and tackle these tomes—and here’s how to do it.

Relax. Ulysses is challenging, but it’s not nearly as challenging as some of Joyce’s other works (did I hear someone scream “Finnegan’s Wake!” in the distance before bursting into tears?). The trick here is to stop trying to comprehend every specific reference to Dublin in 1904 and just get into the rhythm of it. In other words, don’t studyUlysses—read it.

The opening chapter of this novel is one of the hardest to crack in fiction, but the secret to The Sound and the Fury is in the fact that all the information you need to figure it out is right there in the story. The trick? Remember that if you take away the technical virtuosity and literary technique, what you have left is a rip-roaring soap opera about a family destroying itself.

The real challenge of Infinite Jest may be its gonzo science-fiction universe. With wheelchair-bound Québécois assassins, years named after consumer products, and women too beautiful to view safely in full daylight, Infinite Jest takes a while to acclimate to. The secret here is to view the book not as a heavy work of literary genius, but as a roiling comedy that uses its ridiculous setting and details to craft a series of darkly hilarious set pieces.

Moby-Dick has the distinction of being perhaps the most well-known novel no one has read. Its reputation for 19th-century density and complex language makes it fearsome. The trick to Moby-Dick? It is hilarious. There are more dirty jokes in this book than you can shake your peg-leg at (see what we did there), and the whaling stuff? Absolutely thrilling, once you get used to the rhythm of the language.

Yes, In Search of Lost Time is easily the longest thing you’ve ever declined to read. What’s remarkable about it is the depth of the personal—you do get the sense of accompanying someone on a sense-memory exploration. The key here is simple: This book is about many things, but chief among them is sex. Start looking for the dirty bits, and before you know it you’ll be in the middle of volume three.

Rambling, complex, and filled with lengthy philosophical detours, this novel is pretty daunting. But rather than being a dour, endless novel, The Brothers Karamazov is a raucous tale of drunkenness, murder, and lust. The trick here is to stop trying to catch every detail and just enjoy the main stories: Mitya’s and Lyosha’s. If you understand what happens to them, everything else falls into place.

It’s time. You’ve been avoiding Gravity’s Rainbow since you were a kid. You’ve been avoiding the endless symbolism, the encyclopedic puns, and the faint sense that Pynchon is pulling our legs. But this is a book you can’t dismiss unless you’ve read it, and it’s time. The trick—as with all of Pynchon’s work—is to stop thinking of the book as an awesome piece of serious literature and just enjoy it as a silly farce. This is, after all, a book that includes a bit about a man whose erections may predict rocket attacks on wartime London.

The language of this book even in translation isn’t complex, and the story it tells isn’t symbolic. The difficulty lies in the subject matter; it’s difficult to imagine that anyone could experience—and survive—what Solzhenitsyn and his fellow prisoners did. The trick here? Every time you finish a page, wiggle your toes inside your slippers and sip something nice and simply be happy it’s a book.

When approaching this book nervously, from an angle, you’ll hear some fairly alarming terms, like semiotics or deliberate mistranslation. Fear not! The trick with this admittedly dense and fascinating novel is simple: It’s a murder mystery. Let everything else hit you subliminally, and just concentrate on enjoying the story at its most primal level.

Cloud Atlas has the difficult novel trifecta: A shattered timeline, an invented patois, and a story involving several sets of characters in completely different time periods. The trick with Cloud Atlas is that it’s like reading seven novels all at once. There is a theme, and a point, but ultimately what this means is that if you’re confused or bored or mildly alarmed by what you’re reading, just muddle through—a new story will begin shortly.

The novels of Thomas Pynchon have generally been considered unfilmable. Dense, chaotic, cerebral—Pynchon’s oeuvre is composed of novels that don’t lend themselves readily to cinematic moments and the condensation required to turn a book into a two-hour (or even three-hour) film. In 2009, however, the odds shifted a bit when Pynchon published Inherent Vice, one of his most accessible and “mainstream” novels ever—and indeed, the film adaptation is being released on December 12 (as the sardonic voiceover in the trailer notes, “just in time for Christmas”).

The film was written and directed by Paul Thomas Anderson, known for Boogie Nights, Magnolia, There Will be Blood, andThe Master. As is often the case with Pynchon’s novels, the revelation of this one fact—Anderson as the writer/director of Inherent Vice—makes everything else click into better focus. Because there is no one else in the world better equipped to write and direct this film. Here’s why.

Anderson is the Film World’s Pynchon
Pynchon writes novels that tell complex and often confounding stories with dense layers of meaning and twisting, unpredictable plots that reward frequent rereads and the occasional bout of research. Anderson creates films that tell complex and often confounding stories with dense layers of meaning and twisting, unpredictable plots that reward frequent rewatching and the occasional bout of analysis. If there’s another director out there more suited to take on Pynchon, I’d like to hear it.

He’s Used to Stories with a Lot of Characters
A Pynchon novel is crowded with a cast of characters that are equal parts mysterious, amusing, and frustrating—just like the crowded films Anderson tends to make. The crowded tableaus of Boogie Nights and Magnolia and even the relatively sparsely populated The Master mark Anderson as one of the few Hollywood directors capable of managing Pynchon’s sprawling list of supporting and minor characters, all of whom have significance requiring careful attention no matter how little they appear on screen.

He Tells Stories that Don’t Make Sense at First. Or at Second.
People have been reading and discussing Pynchon’s novels for decades now. Inherent Vice is certainly one of the most accessible of Pynchon’s novels, but it remains more challenging than most books. Anderson’s films have inspired a similar level of discussion, from the meaning of the number 82 referenced throughout Magnolia, to whether or not the Master actually spoke in Freddie’s dream, to what the push-in on the tiny note declaring “but it did happen” meant, again in Magnolia. Anderson is used to weaving clues and thoughtful references into his films, making him the ideal choice to work with someone of Pynchon’s complexity.

Anderson’s Other Works Explores the Concept of ‛Inherent Vice’
The phrase “inherent vice” only appears in one other Pynchon novel, but its meaning is thematically explored in both Pynchon’s novels and Anderson’s films. The phrase means the unavoidable flaw in anything that is often unnoticed at first but which dooms everything to eventual ruin and destruction, no matter how nobly conceived or carefully constructed. One layer of the book explores the last gasp of California’s underground drug culture as it sours into the 1970s, and Anderson’s films often tell a story of a golden age descending into madness and chaos.

Anderson’s Good at Sprawl
Anderson’s films all have the feel of an epic, even if the stories they tell are small on the surface. The same could be said of Pynchon, who often takes small-scale plot (such as a woman trying to settle an ex-lover’s estate) and sprawls it out into a huge adventure covering plenty of geographic and conceptual ideas. The eccentric detective story of Inherent Vice seems like the plot of an Anderson movie that just hadn’t been made yet, except of course now it has and that is possibly the most Pynchonesque/Anderson-like thing to ever happen.

In the end, if you’ve been curious about Pynchon but intimidated by the scale and complexity of his work, Inherent Vice might be the perfect place for you to start. Yes, some of Pynchon’s older works are shorter—but this book has the most conventional structure and storytelling in Pynchon’s oeuvre, making it the Pynchon gateway drug (which is appropriate, given the book’s setting in the closing days of the southern California drug scene’s Golden Age). But if you’re going to watch the film first, you can rest assured the perfect director will be working with the material.

If you’ve been conscious at any time in the last century or so, you’re familiar with private detective tropes: the hardboiled operator who’s as quick with a biting quip as he is with a hand cannon, always getting mixed up with the wrong kind of girl as he doggedly follows the clues.

At least, that’s the typical detective. Over the years there have been some notable exceptions to this mold, detectives who are recognizably in a detective story but either don’t play the part at all, or find themselves involved in truly unusual mysteries. If you’re looking to mix up your detective story habit, here are five oddballs who will satisfy your yen for mystery and your yen for surprisingly creative worlds.

Inherent Vice, by Thomas Pynchon
Pynchon doesn’t really “do” plots, does he—at least not plots that make any sense in the conventional way. Which makes his decision to write a story structured similarly to a classic private eye story a fascinating one, but it works perfectly. Slacker/stoner detective Doc Sportello is an incredible entry in the category of literary detectives because he’s practically his own client: suffering from memory problems, apparent narcolepsy, and a myriad of other problems staying in sync with the real world, Sportello’s an unreliable narrator, seems aware of the fact, and isn’t troubled by it. While the central mystery is just a way for Pynchon to riff brilliantly for a few hundred pages, there’s a detective story at the core of this sprawling novel—one whose solution will surprise and challenge you. The book also serves as a lament of sorts for a moment in American history when it seemed like the Freaks were winning, which slots right in with the countercultural vibe of most detectives in modern literature.

Gun, with Occasional Music, by Jonathan Lethem
While most people seem to have forgotten or overlooked Lethem’s debut, it’s an absolute treat for anyone who loves a good detective novel and has a penchant for the absurd. In a sci-fi world where questions are considered rude and you can be punished for rudeness, how can a private detective work? The detective aspects of the story have a clear link back to Chandler, Hammett, and other classic detective novels, but the greatest trick Lethem has ever pulled (so far) is somehow making a kangaroo in a dinner jacket (an inspiration taken directly from a line in one of Chandler’s lesser works) feel completely organic to the story.

Dirk Gently’s Holistic Detective Agency, by Douglas Adams
While everyone remains aware of The Hitchhiker’s Guide to the Galaxy, Adams’ other major novels, the two Dirk Gently books, get much less attention. Which is a shame, as they are brilliant. Gently is a “holistic” detective who disdains merely solving one aspect of a crime. Since everything is connected, he seeks to solve the “whole” crime. Even better, Gently is a psychic who denies being psychic and claims to simply be very, very good at guessing. As with all Adams’ novels, the best bits are the throwaways—like a couch that gets stuck in a stairwell despite it being technically impossible for the couch to be stuck in that particular way according to the laws of physics—but what really makes the Gently books great is the fact that these classic Adams throwaway gags aren’t throwaways. They all circle back and tie together in insane but spectacular ways.

The Yiddish Policemen’s Union, by Michael Chabon
This fantastic novel is an alternative history novel, and what truly sets it apart from just about every novel ever written is how well it’s constructed. The alternative timeline, wherein Israel is destroyed in 1948 and a temporary Jewish settlement in Alaska becomes the Jewish state (something that almost happened) is simultaneously subtle and ambitious in scope. Add in a mystery that’s well-constructed just as a mystery, a long list of creative and fascinating characters (and genius riffs on one of the world’s most musical languages, Yiddish), and you’ve got a tremendous book that also happens to be an oddball detective novel.

The Robots of Dawn, by Isaac Asimov
The third book in Asimov’s Robot trilogy, Asimov explodes both science fiction and detective novel tropes in a story that combines domed cities, a human population struggling with an ingrained fear of outdoor space, robot technology, and space opera politics—and that doesn’t even touch on the actual mystery. What’s truly remarkable about the book (and the trilogy in general) is how Asimov makes the detective novel fit so well into the sci-fi novel, creating a rare breed: a mixed-genre book where almost no seams show. Also remarkable? Robots of Dawn was published 26 years after the second book in the trilogy, but you wouldn’t know it from the prose, which is as fresh and exciting as Asimov’s best.

There’s no TV show quite as quoted or as quotable as The Simpsons, the evergreen Fox animated sitcom that’s been on television since George Bush was president (no, the other one). Though my wife rarely appreciates my perfectly timed Mr. Burns bon mots, there are a whole lot of us who could probably converse for an entire day in nothing but Simpsons quotes.

The show is especially beloved by those with nerdish…leanings, as over the past few decades it has become the hotspot for cameo appearances by a host of famous authors. For all we know, Thomas Pynchon hasn’t left his bathrobe since 1971, but he’s been on The Simpsons twice, albeit with an animated paper bag over his head (he even blurbed Marge’s book: “Thomas Pynchon loved this book almost as much as he loves cameras!”). Thanks to Lisa Simpson, I knew Gore Vidal’s name long before I knew who Gore Vidal was (“These are my friends! Grown-up nerds like Gore Vidal, and even he’s kissed more boys than I ever will!”)

In honor of the FXX Network’s ongoing 12-day marathon of every. Episode. Ever (all 552 of ‘em), which kicked off yesterday, I present to you the top 5 author cameos in the show’s storied history. (Excluding Pynchon, because landing not one, but two appearances by the world’s most reclusive author is hard to top.)

5. J.K. Rowling (Episode: The Regina Monologues, Season 15)
At the height of Potter-mania, Harry Potter’s creator made a memorable appearance in an episode in which the Simpson family travels to England on vacation. Lisa asks her what will happen at the end of the series, to which the exasperated author responds, “He grows up and marries you. Is that what you want to hear?” Lisa: “[sigh] Yes!”

4. James Patterson (Episode: Yokel Chords, Season 18)
From the few glimpses we’ve gotten, Marge Simpsons has a deeply weird fantasy life, a fact that was never so clear as the time she fell asleep on the beach reading Kiss the Girls and had a sexy dream about James Patterson riding in on a white steed to sweep her away. (“Come with me, Marge. Help me think of new nursery rhyme-themed titles for my thrillers.”)

3. Amy Tan (Episode: Insane Clown Poppy, Season 12)
The Springfield Festival of Books manages to attract some pretty big-name authors, including Stephen King and Maya Angelou (who recites a poem about a B-2 bomber for some reason), but my favorite bit in this cameo-heavy outing involves Amy Tan’s reaction to Lisa’s interpretation of The Joy Luck Club (“No, that’s not what I meant at all. You couldn’t have gotten it more wrong. Please just sit down. I’m embarrassed for both of us.”).

1. Neil Gaiman (Episode: The Book Job, Season 23)
In an entire episode devoted to parodying the trends in the new industry of YA mega-hits like Harry Potter and Twilight, Gaiman steals the show, literally, and wins the award for least self-aggrandizing cameo appearance ever in the bargain. Homer and his friends collaborate on a surefire-hit YA novel about magical trolls, and Gaiman agrees to help them write it (though mostly they let him pick up the sandwiches). At the end of an Ocean’s 11-style caper that involves rescuing the manuscript for The Troll Twins of Underbridge Academy from the unscrupulous publisher, it is revealed that Gaiman has absconded with the only copy and published it under his own name, winning yet another literary award despite the fact that he is illiterate.